ABSOLUTE CONFIGURATION OF (2R,3R,6S,8R)-METHYL HOMONONACTATE, A POLYKETIDE FROM ACTINOMYCETES Streptomyces sp R-527F OF THE ARCTIC REGION
ABSOLUTE CONFIGURATION OF (2R,3R,6S,8R)-METHYL HOMONONACTATE, A POLYKETIDE FROM ACTINOMYCETES Streptomyces sp R-527F OF THE ARCTIC REGION
复制标题
北极地区放线菌链霉菌 R-527F 聚酮化合物 (2R,3R,6S,8R)-高单乙酸甲酯的绝对构型
DOI：
10.1007/s10600-018-2488-7
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发表时间：
2018
影响因子：
0.8
通讯作者：
Guo Yue-Wei
中科院分区：
文献类型：
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作者：
Ye Fei;Cai Meng-Hao;Chen Bo;Xiao Wei;Li Xu-Wen;Guo Yue-Wei
自从1908年Ekelof首次在南极地区发现和分离微生物以来，由于极低温、高盐度和强辐射等特殊的生存环境，对极地微生物的微生物、生态学和化学研究成为热点[1，2]。从极地地区的微生物中发现了各种天然产物，如萜类化合物、生物碱和聚酮类化合物，具有广泛的生物活性，包括细胞毒性、抗病毒活性等。其中，大四内酯型聚酮因其高度的化学复杂性和生物多样性而备受关注[5-7]。事实上，大四内酯类化合物是由几个非乳酸对映体或其同系物以(+)(-)(+)(-)-酯连接而成的环状聚醚家族，这种有趣的分子拓扑结构在其他天然产物中很少观察到[8]。在寻找海洋微生物产生的新的生物活性代谢物[9，10]的过程中，特别是来自北极地区的海洋微生物产生的生物活性聚醚，链霉菌sp.R-527F是从楚科奇海陆坡(73q59.929cN，169q00。272cW，173米)，由中国科学考察队在2008年进行。在以前的药理研究中，该菌株的发酵液对金黄色葡萄球菌、枯草芽孢杆菌和大肠杆菌具有抗菌活性[11]。因此，在本工作中进行了生物活性导向的分离，从而发现了7种次生代谢物，包括一个含有四氢呋喃的聚酮，(2R，3R，6S，8R)-高N-甲酸甲酯(1)，一个苯甲酰胺衍生物2-丙酮氨基苯甲酰胺(4)，以及5个已知的DKPs(二酮基哌嗪)(5-9)。这是首次报道由极地微生物产生的含有四氢呋喃的聚酮。在这里，我们描述了化合物1的分离、绝对构型、鉴定和生物活性。
Since the first report of the discovery and separation of microbes by Ekelof in the Antarctic region in 1908, the microbiological, ecological, and chemical studies of the strains from polar regions have become a hotspot due to the special living environments of the microorganisms, such as extremely low temperature, high salinity, and intense radiation [1, 2]. Diverse natural products, such as terpenoids, alkaloids, and polyketides, with a wide range of biological activities, including cytotoxicity, antiviral activity, etc., were found from microbes of the polar regions [3, 4]. Among them, macrotetrolide type polyketides have attracted a lot of attention thanks to their high chemical complexity and biological diversity [5–7]. In fact, macrotetrolides are a family of cyclic polyethers biosynthetically derived from several molecules of enantiomeric nonactic acid or its homologs with a (+)(–)(+)(–)-ester connection, an intriguing molecular topology seldom observed in other natural products [8].In the course of searching for novel bioactive metabolites [9, 10] such as marine bioactive polyethers, produced by the marine microbes, especially from the Arctic region, the strain Streptomyces sp. R-527F was separated from marine sediment samples collected in the continental slope of Chukchi Sea (73q59. 929cN, 169q00. 272cW, 173 m) by the China scientific expedition in 2008. In the previous pharmacological research, the fermentation broth of this strain exhibited antibacterial activity against Staphylococcus aureus, Bacillus subtilis, and Escherichia coli [11]. Therefore, the bioactivity-guided isolation was conducted in this work, leading to the discovery of seven secondary metabolites, including a tetrahydrofuran-containing polyketide,(2R, 3R, 6S, 8R)-methyl homononactate (1), a benzamide derivative 2-pyruvylaminobenzamide (4), and five known DKPs (diketopiperazines)(5–9). This is the first report of a tetrahydrofuran-containing polyketide produced by microorganisms from the polar region. Herein we describe the isolation, absolute configuration, elucidation, and bioactivities of compound 1.